76735-48-3

Basic information

• Product Name: Benzoic acid 3-{2-[3-(1,1-dimethyl-prop-2-ynyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester
• Synonyms: Benzoic acid 3-{2-[3-(1,1-dimethyl-prop-2-ynyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester
• CAS NO: 76735-48-3
• Molecular Weight: 444.527
• Mol File: 76735-48-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzoic acid 3-{2-[3-(1,1-dimethyl-prop-2-ynyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid 3-{2-[3-(1,1-dimethyl-prop-2-ynyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester(76735-48-3)
• EPA Substance Registry System: Benzoic acid 3-{2-[3-(1,1-dimethyl-prop-2-ynyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester(76735-48-3)

Safety Data

• Hazardous Substances Data: 76735-48-3(Hazardous Substances Data)

Upstream product

• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 76735-49-4 5-benzoyloxy-3'-hydroxy-3,4'-dimethoxydihydrostilbene 
• 621-59-0 isovanillin 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 19270-10-1 benzoyl cation 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 83088-05-5 3-hydroxy-5-methoxybenzyltriphenylphosphonium bromide 
• 83088-21-5 3-(β-methoxyethoxymethyloxy)-4-methoxybenzaldehyde 
• 91925-81-4 3-(bromomethyl)-5-methoxyphenol 
• 76735-47-2 Benzoic acid 3-[(E)-2-(3-benzyloxy-4-methoxy-phenyl)-vinyl]-5-methoxy-phenyl ester 
• 76735-46-1 3'-benzyloxy-5-hydroxy-3,4'-dimethoxystilbene 
• 19520-74-2 3-hydroxy-5-methoxy-benzoic acid methyl ester 

Downstream Products

• 70677-47-3 canniprene 
• 76735-51-8 Benzoic acid 3-{2-[3-hydroxy-4-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-ethyl}-5-methoxy-phenyl ester 
• 76735-50-7 Benzoic acid 3-{2-[3-(1,1-dimethyl-allyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester 

Relevant articles and documents

Dihydrostilbenes of Cannabis. Synthesis of Canniprene

Canniprene (10) is synthesised via reaction of a phenolate-anion ylide with a benzyl-protected aldehyde.Benzoylation, followed by hydrogenation and hydrogenolysis of the resulting stilbene, leads to a half-benzoylated bibenzyl which is converted into its O-dimethylprop-2-ynyl derivative.Semi-hydrogenation, Claisen rearrangement, and debenzoylation gives canniprene.In a second synthesis the prenylated (3-methylbut-2-enylated) and benzyl-protected ring-B section is made first and converted by Wittig reaction into a dibenzyl-protected stilbene.The stilbene is reduced and the benzyl groups removed in one step, without affecting the prenyl group, by sodium in butanol: magnesium in methanol is capable of stilbene reduction without debenzylation.This practical synthesis proceeds in 19 percent overall yield from the dimethylprop-2-ynyl ether of isovanillin (14) and is applicable to isotopelabelling.The use of p-bromophenacyl (PBP) ether and methoxyethoxymethyl (MEM) ether protection as the basis for canniprene synthesis is also considered.Other bibenzyls relevant to the natural products of Cannabis are made and the methylated chroman (37) derived from canniprene is also synthesised.